Classifications

• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
• • A—HUMAN NECESSITIES
  • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
  • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
  • A01N39/00—Biocides, pest repellants or attractants, or plant growth regulators containing aryloxy- or arylthio-aliphatic or cycloaliphatic compounds, containing the group or, e.g. phenoxyethylamine, phenylthio-acetonitrile, phenoxyacetone
• • A—HUMAN NECESSITIES
  • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
  • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
  • A01N39/00—Biocides, pest repellants or attractants, or plant growth regulators containing aryloxy- or arylthio-aliphatic or cycloaliphatic compounds, containing the group or, e.g. phenoxyethylamine, phenylthio-acetonitrile, phenoxyacetone
  • A01N39/02—Aryloxy-carboxylic acids; Derivatives thereof
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
  • C07C41/48—Preparation of compounds having groups
  • C07C41/50—Preparation of compounds having groups by reactions producing groups
  • C07C41/56—Preparation of compounds having groups by reactions producing groups by condensation of aldehydes, paraformaldehyde, or ketones
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
  • C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
  • C07C45/511—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups
  • C07C45/515—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups the singly bound functional group being an acetalised, ketalised hemi-acetalised, or hemi-ketalised hydroxyl group
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
  • C07C45/56—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds
  • C07C45/57—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with oxygen as the only heteroatom
  • C07C45/58—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with oxygen as the only heteroatom in three-membered rings
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C47/00—Compounds having —CHO groups
  • C07C47/20—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms
  • C07C47/277—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms containing ether groups, groups, groups, or groups
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
  • C07C49/20—Unsaturated compounds containing keto groups bound to acyclic carbon atoms
  • C07C49/255—Unsaturated compounds containing keto groups bound to acyclic carbon atoms containing ether groups, groups, groups, or groups
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
  • C07C57/52—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing halogen
  • C07C57/58—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing halogen containing six-membered aromatic rings
  • C07C57/60—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing halogen containing six-membered aromatic rings having unsaturation outside the rings

Definitions

• This invention relates to 4-phenoxy-2-butene derivatives, their use as plant growth regulating agents and to plant growth regulating compositions of said compounds.
• R 1 and R 2 are selected from hydrogen and -CH 3 with the proviso that one of R 1 and R 2 is -CH 3 and the other is hydrogen;
• R 3 is selected from the group consisting of hydrogen, hydroxy, (lower)alkyl, amino, -O-(lower)alkyl, -S-(lower)alkyl, -NH-(lower)alkyl, or -N-di(lower)alkyl;
• Y is selected from the group consisting of (lower)alkyl, halo, nitro, -CF 3 , -S-(lower)alkyl, -O-(lower)alkyl, -O-acetyl, hydroxy, -NH-acetyl, amino, -NH(lower)alkyl, -N-di(lower)alkyl, and
• (lower)alkyl as used in the foregoing definitions is meant to include straight or branched chain alkyl radicals containing from 1 to 6 carbon atoms, such as, for example, methyl, butyl, hexyl, 1-methylethyl and the like.
• the halo atom can be any suitable halogen atom
• Y is preferably chlorine or bromine.
• the phytopharmaceutically acceptable salts can be salts of the appropriate derivatives with inorganic or organic acids, such as, for example, hydrochloric, nitric, sulfuric, I chloric, thiocyanic, phosphoric, acetic, p-toluenesulfonic, oxalic, methanesulfonic, ethanesulfonic, naphthalenesulfonic acid and the like.
• inorganic or organic acids such as, for example, hydrochloric, nitric, sulfuric, I chloric, thiocyanic, phosphoric, acetic, p-toluenesulfonic, oxalic, methanesulfonic, ethanesulfonic, naphthalenesulfonic acid and the like.
• the 4-phenoxy-2-butene derivatives and phytopharmaceutically acceptable salts thereof inhibit cytokinin plant growth regulating activity and also seed germination regulatory properties or senescence delaying activity when applied to plants in plant growth regulating amounts.
• the 4-phenoxy-2-butene derivatives and phytopharmaceutically acceptable salts thereof have also been found to possess plant dwarfing activity when applied to plants in plant dwarfing effective amounts and herbicidal activity when applied in herbicidally effective amounts.
• the 4-phenoxy-2-butene derivatives of thsi invnetion have been found to possess plant growth regulating activity when ampolyed in effective plant growth regulating amounts.
• the compounds of the present invention are gunerally active plant growth regulants when applications of frow about employed and preferably from about 0.1 kg to about 5 kg/ beceare.
• R 1 and R 2 are selected from hydrogen and -CH 3 with the proviso that one of R 1 and R 2 is -CH 3 and the other is hydrogen;
• R 3 is selcted from hydrogen, hydroxy and -O-(lower)alkyl;
• Y is selected from the group sonelstin of naio, -O-(lower)-alkyl, -O-acetyl, hydroxy, -NH-acetyl and a fused benzene ring; and n is equal to 1 or 2, preferably 1. It is also preferred that when Y is halo, Y is chlorine and then preferably n is equal to 2 and the Y's are in the 2- and 4- positions on the phenyl ring.
• R 3 is -O-(lower)-alkyl
• R 3 is hydrogen
• Oxidation of the aldehyde is accomplished, for example, by the use of a manganese dioxide/sodium cyanide oxidation reaction system in the presence of acetic acid and methanol.
• R 3 is hydroxy
• the compounds of this invention wherein R 3 is hydroxy may be prepared, for example, by the base catalyzed hydrolysis of the corresponding compound wherein R 3 is -O-(lower)-alkyl. Hydrolysis of the compound wherein R 3 is -O-(lower)-alkyl is accomplished, for example, by the use of a 20% solution of potassium hydroxide in methanol.
• R 3 is amino, -NH-(lower)alkyl, -N-di(lower)alkyl or -S-(lower)alkyl
• R 4 is Cl
• the reaction is also run in the presence of N,N-dicyclohexylcarbodiimide.
• reaction scheme is as follows: wherein R 4 is OH or Cl and R 3 is amino, -NH-(lower)alkyl, -N-di(lower)alkyl or -S-(lower)alkyl and R 3 R 2 Y and n are as first defined hereinbefors.
• the benzene extract is concentrated and vacuum dried to give 0.75 g of (E)-4-(4-acetylaminophenoxy)-1,1-diethoxy-2-methyl-2-butene which is dissolved in about 5 to 10 ml acetone and treated with about 1 ml water and a spatula of p-toluenesulfonic acid monohydrate.
• the resulting.solution is agitated occasionally for 30 minutes and the solution is evaporated at room temperature giving a solid, ethylether insoluble residue.
• the residue is dissolved in about 150 ml methylene chloride and washed twice with water. The residue is dried with sodium sulfate and concentration gave 0.45 g of a solid.
• Acetone is then stripped at room temperature.
• the residue is treated with 75 ml benzene and 75 ml methylene chloride.
• This mixture is extracted with 70 ml of 10% aqueous potas- siam carbonate.
• the lower organic layer is drawn off and the agueous layer plus emulsion is extracted with two 75 ml portions of methyleue chloride.
• the organic phases are combined, washed once with about 75 ml water and dried with sodium sulfate. Concentration gives 4.1 g solid residue.
• the filtrate is evaporated to dryness and the yellow-brown oil is taken up in a mixture of 120 ml acetone and 20 ml water and stirred under nitrogen as 3.0 g p-toluenesulfonic acid is added. Thirty minutes after the addition, the solution is evaporated to dryness and the residue taken up in 200 ml diethylether and this solution washed with two 200 ml portions deionized water. The ether solution is treated with magnesium sulfate and activated carbon and then filtered. The filtrate is evaporated to dryness to yield 31.47 g purple oil which is purified by chromatography on a Waters Prep.
• the organic phase is washed with three 100 ml portions of water, dried over magnesium sulfate and filtered.
• the filtrate is evaporated to dryness to yield 2.71 g of oily yellow solid residue.
• the residue is dissolved in 50 ml hot ether and the solution heated under a stream of nitrogen as 10 ml hexane is added. When the volume of the solution reaches 40 ml, it is filtered through a 1 cm column of silica gel in a 30 cc fritted glass filter. The filtrate is placed in a freezer and a white crystalline solid forms which is collected by nitrogen pressure filtration-and washed with 10 ml of a 1:1 mixture of ether and hexane.
• the mixture is extracted with by 10 ml portions of mothylane chloride and the ex- turots are combined and treated with magnesinm sulfate and the mixture filtered.
• the filtrate is heated under a stream of mitregon as 5 ml of bernne is added. When the volume resches 10 ml the solution is allowed to cool to room temperature and is placed in a freezer. A white needle-like product is collected, m.p. 117-121, 5°C.
• the solution is then extracted with two 200 ml portions of diethylether and the extracts combined, washed with four 500 ml portions of deionized water and the extracts combined, washed with four 500 ml portions of distilled water, dried with mangesium sulfate and treated with activated charcoal.
• the solution is filtered and the filtrate evaporated to dryness to yield 8.53 g of a yellow-brown oil.
• the oil is dissolved in 60 ml of a 1 to 5 water-acetone mixture and the solution stirred under nitrogen as 1.0 g p-toluenesulfonic acid monohydrate is added and the solution is stirred at room temperature for about one hour and evaporated to dryness.
• reaction mixture is stirred for 21 ⁇ 2 hours at room temperature and is then poured into 700 ml 10% potassium carbonate at 0°C
• the mixture is extracted with two 200 ml portions of diethylether and the extracts are combined and washed with four 200 ml portions of distilled water.
• Anhydrous mag- four 200 ml portions of distilled water Anhydrous mag- uesium sulfate and activated charcoal are added to the solution and it is allowed to stand for 30 minutes and is than riltered.
• the golden filtrate is evaporated to dryaess to yield 11.36 g of dark yellow brown il which is (E)-463- acstoxyplanoxy)-1,1-dietnoxy-2methyl which is dissoived in 150 ml methanol and stirred under nitrogen as stirred for abort two hours.
• the reactive mixtare is placed in a rotary evaporator ana the methanol removed.
• the remaining mixture is diluted to 200 ml and extrated ml diethylether.
• the ether solution is evaporated to dryness.
• the solution is dried over magnesium sulfate and treated with activated charcoal and filtered to yield a bright yellow solution.
• the solution is evaporated and yields 3.41 g of yellow oily residue which is taken up in 30 ml of a 1:5 water-acetone mixture and stirred under nitrogen as 0.5 g p-tolunesulfonic acid monohydrate is added. After about 30 minutes, the solution is evaporated to dryness and 25 ml water and 25 ml ethyl acetate are added and the residue separated. The ethyl acetate phase is dried over magnesium sulfate, treated with activated charcoal and filtered and the filtrate evaporated to dryness to yield 2.5 g yellow, oily solid residue.
• the compounds of this invention have plant growth regulating activities.
• the plant growth regulating effects are manifested as for example a stunting or dwarfing effect on the vegetative growth of plants.
• Such stunting or dwaifin may be useful, for example, in peanuts, cereals and soya bean where reduction in stem growth may reduce the risk of lodging and may also permit increased amounts of fertilizer to be applied.
• the stunting of woody species is useful in controlling the growth of undergrowth under power lines and the like.
• Compounds which induce stunting or dwarfing may also be useful in modifying the stem growth of sugar cane thereby increasing the concentration of sugar in the cane at harvest; in sugar cane, the flowering and ripening may be controllable by applying the compounds Stunting of peanuts can assist in harvesting.
• the compounds may stunt grasses without significant phytotoxic effects and without deleteriously affecting the appearance, particularly the color, of the grass. This makes such compounds attractive for use on ornamental lawns and on grass verges. They may also have an effect on flower head emergence in for example grasses.
• the compounds may also stunt weed species present in the grasses; examples of such weed species are sedges such as Cyperus spp. and dicotyledonous weeds, for example, daisy, plantain, knotweed, speedwell, thistle, docks and ragwort.
• non-crop vegetation for example, weeds or cover vegetation
• weeds or cover vegetation may be retarded thus assisting in the maintenance of plantation and field crops.
• fruit orchards particularly orchards subject to soil erosion
• the presence of grass cover is important.
• excessive grass growth requires substantial maintenance.
• the compounds of the invention could be useful in this situation as they could restrict growth without killing the plants which would lead to soil erosion.
• the degree of competition for nutrients and water by the grass would be reduced and this could result in an increased yield of fruit.
• one grass species may be stunted more than another grass species; this selectivity could be useful for example for improving the quality of a sward by preferential suppression of the growth of undesirable species.
• the dwarfing may also be useful in miniaturizing ornamental, household, garden and nursery plants, for example, poinsettias, chrysanthemums, carnations, tulips and daffodils.
• the compounds may also be used to stunt woody species. This property may be used to control hedgerows or to shape fruit trees, for example, apples.
• the plant growth regulating effect may, as implied above, manifest itself in an increase in crop yield.
• vine control in the field and inhibition of sprouting in the store may be possible.
• Other plant growth regulating effects caused by the compounds may include alteration of leaf angle and promotion of tillering in plants.
• the former effect may be useful for example in altering the leaf orientation of, for example, ; potato crops thereby letting more light into the crops and inducing an increase in photosynthesis and tuber weight.
• by increasing tillering in mono- and dicotyledonous crops, for example, rice, corn and soybeans the number of flowering shoots per unit area may be increased thereby increasing the overall grain of such crops. In grass swards an increase in tillering could lead to a denser sward which may result in increased resilience in wear.
• the treatment of plants with the compounds may lead to the leaves developing a darker green color and delay senescence in crops thereby leading to improved pod fill in sey bean for example.
• the compounds may inhibit, or at least delay, the flowering of sugar beet and thereby may inciease sugar yield. They may also reduce the size of sugar beet without reducing significantly the sugar yield thereby enabling an increase in planting density to be made. Similarly, in other root crops, such as, for example, turnip, swede, mangold, parsnip, beetroot, yam and cassava, it may be possible to increase the planting density.
• the compounds could be useful in restricting the vegetative growth of cotton thereby leading to an increase in cotton yield.
• the compounds may be useful in rendering plants resistant to stress since the compounds may delay the emergence of plants grown from seed, shorten stem height and delay flowering. These properties could be useful in preventing frost damage in countries where there is significant snow cover in the winter since then the treated plants would remain below the snow cover during the cold weather. Further the compounds may provide drought or cold resistance in certain plants.
• the amount of compound to be applied to regulate the growth of plants will depend upon a number of factors, for example the particular compound selected for use, and the identity of the plant species whose growth is to be regulated. However, in general an application rate of 0.05 to 20, preferably 0.1 to 5, kg per hectare is used. However, on certain plants even application rates within these ranges may give undesired phytotoxic effects. Routine tests may be necessary to determine the best rate of application of a specific compound for any specific purpose for which it is suitable.
• the compounds may be used as such plant growth regulating purposes but are more conveniently formulated into compositions for such usage.
• the invention thus provides also a plant growth regulating composition comprising a compound of Formula 1 or 2 or a phytopharmaceutically acceptable salt thereof as hereinbefore defined, and an inert carrier or diluent.
• the plant growth regulating compounds of this invention can be applied in a number of ways, for example they can be formulated or unformulated, directly to the foliage of a plant, or they can be applied also to bushes and trees, to seeds or to other media in which plants, bushes or trees are growing or are to be planted, or they can be sprayed on, dusted on or applied as a cream or paste formulation, or they can be applied as a vapor. Applieation can be to any part of the plant, bush or tree, for example to the foliage, stems, branches or roots, or to soil surrounding the roots, for systemic activity, or to the saed berere it is pllante
• plant as used herein includes seedlings, bushes and trees.
• the compounds are preferably used for agricultural and horticultural purposes in the form of a composition.
• the type of composition used in any instance will depend upon the particular purpose envisaged.
• compositions may be in the form of dusting powders or granules comprising the active ingredient and a solid diluent or carrier, for example fillers such as kaolin, bentonite, keiselguhr, dolomite, calcium carbonate, talc, powdered magnesia, Fuller's earth, gypsum Hewitt's earth, diatomaceous earth and China clay.
• a solid diluent or carrier for example fillers such as kaolin, bentonite, keiselguhr, dolomite, calcium carbonate, talc, powdered magnesia, Fuller's earth, gypsum Hewitt's earth, diatomaceous earth and China clay.
• Such granules can be preformed granules suitable for application to the soil without further treatment.
• These granules can be made either by impregnating pellets of filler with the active ingredient or by pelleting a mixture of the active ingredient and
• compositions for dressing seed may comprise an agent, for example a mineral oil, for assisting the adhesion of the composition to the seed.
• an agent for example a mineral oil
• the active ingredient can be formulated for seed dressing purposes using an organic solvent, for example N-methylpyrrolidone or dimethylformamide.
• compositions may also be in the form of dispersible powders, granules or grains comprising a wetting agent to facilitate the dispersion in liquids of the powder or grains which may contain also fillers and suspending agents.
• aqueous dispersions or emulsions may be prepared by dissolving the active ingredient in an organic solvent optionally containing wetting, dispersing or emulsifying agents and then adding the mixture to water which may also contain wetting, dispersing or emulsifying agents.
• organic solvents there may be mentioned, for example, ethylene dichloride, isopropyl alcohol, propylene glycol, diacetone alcohol, toluene, kerosene, methylnaphthalene, the xylenes, trichloroethylene, furfuryl alcohol, tetrahydrofurfuryl alcohol, and glycol ethers such as 2-ethoxyethanol and 2-butoxyethanol.
• compositions to be used as sprays may also be in the form of.aerosols wherein the formulation is held in a container under pressure in the presence of a propellant, such as, for example, fluorotrichloromethane or dichlorodifluoromethane.
• a propellant such as, for example, fluorotrichloromethane or dichlorodifluoromethane.
• the plant growth regulating compounds can be mixed in the dry state with a pyrotechnic mixture to form a composition suitable for generating in enclosed spaces a smoke containing the compounds.
• the compounds may be used in a micro-encapsulated form.
• the different compositions can be better adapted for various utilities.
• the plant growth regulating compounds can also be used as mixtures with fertilizers.
• Compositions comprising only granules of fertilizer incorporating, for example coated with, the plant growth regulating compound, are preferred. Such granules suitably contain up to 25% by weight of the compound.
• the invention therefore also provides a fertilizer composition comprising the plant growth regulation compound of Formula 1.
• compositions may also be in the form of liquid preparations for use as dips or sprays which are generally aqueous dispersions or emulsions containing the active ingredient in the presence of one or more surfactants, for example, wetting agents, dispersing agents, emulsifying agents or suspending agents.
• surfactants for example, wetting agents, dispersing agents, emulsifying agents or suspending agents.
• agents can be cationic, anionic or non-ionic agents.
• Suitable cationic agents are quaternary ammonium compounds, for example cetyltrimethylammonium bromide.
• Suitable anionic agents are soaps, salts of aliphatic monoesters of sulfuric acid, for example sodium lauryl sulfate, and salts of sulfonated aromatic compounds, for example sodium dodecylbenzenesulfonate, sodium, calcium or ammonium lignosulfonate, butylnaphthalene sulfonate, and a mixture of sodium diisopropyl- and triisopropyl-naphthalene sulfonates.
• Suitable non-ionic agents are the condensation products of ethylene oxide with fatty alcohols such as oleyl or cetyl alcohol, or with alkyl phenols such as octyl- or nonylphenol and octylcresol.
• Other non-ionic agents are the partial esters derived from long chain fatty acids and hexitol anhydrides, the condensation products of the acid partial esters with ethylene oxide, and the lecithins.
• Suitable suspending agents are hydrophilic colloids, for example polyvinylpyrrolidone and sodium carboxymethylcellulose, and the vegetable gums, for example gum acacia and gum tragacanth.
• compositions for use as aqueous dispersions or emulsions are generally supplied in the form of a concentrate containing a high proportion of the active ingredient.
• the concentrates are then diluted with water before use.
• These concentrates often should be able to withstand storage for prolonged periods and after such storage be capable of dilution with water in order to form aqueous preparations which remain homogeneous for a sufficient time to enable them to be applied by conventional spray equipment.
• the concentrates may conveniently contain up to 95%, suitably 10-85%, for example 25-60%, by weight of the active ingredient.
• concentrates suitably contain organic acids, for example, alkaryl or aryl sulfonic acids such as xylenesulfonic acid or dodecylbenzenesulfonic acid, since the presence of such acids can increase the solubility of the active ingredient in the polar solvents often used in the concentrates.
• the concentrates suitably contain also a high proportion of surfactants so that suffisiently stable emulsions in water can be obtained. After dilution to form aqueous preparations, such preparations may contain varying amounts of the active ingredient depending upon the initended purpose, but an aqueous preparation containing 0.0005% or 0.01% to 10% by weight of active ingredient may be used.
• compositions of this invention can comprise also other compounds having biological activity, for example, compounds having similar or complementary plant growth regulating activity or compounds having herbicidal or insecticidal or fungicidal ivtivity.
• the fungicidal compound can be for example one which is capable of combatting ear diseases of cereals such as wheat, seed and soil borne diseases and downy and powdery mildews on grapes and powdery mildew and scab on apple and the like.
• the other fungicidal compounds are imazalil, benomyl, carbendazim (BCM), thiophanate-methyl, captafol, captan, sulphur, dithiocarbamates, carbathiins, copper oxychloride, triforine, dodemorph, tridemorph, dithianon, pyrazophos, binapacryl, quinomethionate, panoctine, furalaxyl, aluminum tris(ethyl phosphonate), DPX3217, ethirimol, di- ; methirimol, bupirimate, chlorothalonil, Chevron RE 20615, vinclozolin, procymidone, iprodione
• the other plant growth regulating compound can be one which controls weeds or seedhead formation, improves the level or longevity of the plant growth regulating activity of the compounds of this invention, selectively controls the growth of the less desirable plants such as grasses or causes the plant growth regulating compound of Formula 1 to act faster or slower as a plant growth regulating agent.
• Some of these other agents will be herbicides.
• suitable agents are the gibberellins such as GA3, GA 4 , or GA 7 , the auxins such as indoleacetic acid, indolebutyric acid, naphthoxyacetic acid or naphthylacetic acid, phenoxyacetic acids such as 2,4- D or MCPA, substituted benzoic acids such as TIBA and morphactins such as chlorfluorecol, and the cytokinins such as kinetin, and benzyladenine, and the cytokinin-like compounds, diphenylurea, and benzimidazole.
• the gibberellins such as GA3, GA 4 , or GA 7
• the auxins such as indoleacetic acid, indolebutyric acid, naphthoxyacetic acid or naphthylacetic acid, phenoxyacetic acids such as 2,4- D or MCPA, substituted benzoic acids such as TIBA and morphactins such as chlorfluorecol
• maleic hydrazide glyphosate, glyphosine, long chain fatty alcohols and acids
• dikegulac substituted quaternary ammonium and phosphonium compounds such as CCC or Phosfon-D, carbetamide, asulam, abscissic acid, isopyrimol, and hydroxybenzonitriles such as bromoxynil.
• Cytokinin type activity is illustrated by a soybean cotyledon callus bioassay test comprising the following procedure.
• Growth medium employed in this test is obtainel in the following manner.
• One liter of growth medium is prepared by adding 10 ml of each of the sixteen following stock solutions to a two liter flask containing 250 ml of water: To said two liter flask is added 30 grams sucrose and the volume is adjusted to 450 ml and to pH 5.8 and thereafter the volume is adjusted to 500 ml with deionized water.
• Flask number 1 is adjusted to 250 ml volume by the addition of deionized water and serves as the growth medium control.
• Flask 2 serves as the kinetin reference standard.
• Deionized water is added to each of flasks 4 through 7 to adjust the volume of each to 250 ml.
• Six petri dishes are prepared by placing the following solutions into the respective dishes. Approximately 1 g of previously cut leaves (for example, 7 to 9 day old wheat, oat or barley, but preferably oat) is floated on the solution in each petri dish. The petri dishes are stored under light of about 25 ft-candles at 27-30°C for approximately seven days. The leaves from each petri dish are then analyzed for the amount of chlorophyll retained in the leaves according to the following procedure. The chlorophyll is extracted from the leaves with several washes of 80% acetone at a total volume equivalent to 1 ml acetone for every 10 mg fresh weight of plant leaves after the last extraction.
• the total volume is adjusted with 100% acetone to accomodate for evaporative loss during extraction.
• Optical density readings on a spectrophotometer are taken of the extract against a solvent blank (80% acetone) at wavelengths of 645 and 663 nm.
• the amount of chlorophyll is calculated with the following equation: Mg total chlorophyll/g

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• Chemical & Material Sciences (AREA)
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• Chemical Kinetics & Catalysis (AREA)
• Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
• Agricultural Chemicals And Associated Chemicals (AREA)

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• 1980
  • 1980-08-14 US US06/178,080 patent/US4340765A/en not_active Expired - Lifetime
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